Related Experiment Video
Updated: Aug 7, 2026

16:24
Controlling the Size, Shape and Stability of Supramolecular Polymers in Water
Published on: August 2, 2012
Do homochiral aggregates have an entropic advantage?
Ryan R Julian1, Sunnie Myung, David E Clemmer
1Department of Chemistry, Indiana University, Bloomington, Indiana 47405, USA.
The Journal of Physical Chemistry. B
|July 21, 2006
Summary
Entropy drives the specific aggregation of chiral molecules. Enantiopure solutions favor specific structures due to lower entropic barriers, a finding supported by amino acid cluster experiments.
Area of Science:
- Chemical Physics
- Supramolecular Chemistry
- Biophysical Chemistry
Background:
- Chiral building blocks form larger aggregates through self-assembly.
- Understanding the driving forces behind selective aggregation is crucial for materials science and drug development.
- Entropy's role in chiral aggregation is not fully elucidated.
Purpose of the Study:
- To investigate the influence of entropy on the aggregation of chiral building blocks.
- To compare model system predictions with experimental data on amino acid clusters.
- To determine if entropy favors homochiral or racemic aggregation.
Main Methods:
- A simple model system was used to analyze entropic effects in chiral aggregation.
- Experimental data from amino acid clusters were compared with model predictions.
- Analysis of cluster abundance and chiral composition in relation to entropic barriers.
Main Results:
- Model predicts enantiopure solutions are more likely to form specific structures due to lower entropic barriers.
- Experimental data on amino acid clusters align with model predictions.
- Unusually abundant clusters were found exclusively in enantiopure solutions, suggesting entropic advantage.
Conclusions:
- Specificity in homochiral clusters is entropically advantageous compared to racemic clusters.
- Entropic effects can outweigh enthalpy changes in determining aggregation preferences.
- Entropy plays a significant role in controlling the self-assembly of chiral molecules.
Related Concept Videos
Chirality in Nature
Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid. The...
Chirality
Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...
Properties of Enantiomers and Optical Activity
It is essential to understand the difference between chiral and achiral interactions and the implications thereof in optical activity and their applications. Just as our feet, which are chiral, interact uniquely with chiral objects, such as a pair of shoes, but identically with achiral socks, enantiomers of a molecule exhibit different properties only when they interact with other chiral media. An example of a significant implication from this facet is the phenomenon known as optical activity,...
Prochirality
The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
Molecules with Multiple Chiral Centers
Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

